


Supernatural Imagines Collection [NSFW]

by eratothemuse



Series: Supernatural Imagines [2]
Category: Supernatural
Genre: Drabble Collection, F/F, F/M, Imagines Collection, M/M, Multi, NSFW, Smut, not safe for work
Language: English
Status: In-Progress
Published: 2018-12-21
Updated: 2019-01-21
Packaged: 2019-09-23 22:42:02
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 67
Words: 14,727
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17089115
Author URL: https://archiveofourown.org/users/eratothemuse/pseuds/eratothemuse
Summary: This is a collection of imagines [from my blog on tumblr - thranduilsperkybutt] involving the Supernatural characters! Only NSFW fic is in this collection, so enjoy! Any additional warnings will be posted in each chapter's Notes.





	1. Gadreel - making you cum by using his grace while you are trying to have a conversation with his brother, Gabriel.

**Author's Note:**

> **Grace kink**

_**Warnings:**  NSFW; Grace kink_

Gif source:  [Gadreel](https://megmeg-chan.tumblr.com/post/160134315097)  |  [Gabriel](https://t.umblr.com/redirect?z=http%3A%2F%2Frebloggy.com%2Fpost%2Fsupernatural-my-stuff-spn-gabriel-richard-speight-jr-spn-gifs-spn-spoilers-spn-p%2F83035156353&t=N2ZiZTQ1NjVjODAwM2JlYjdkOTE0OWRkZTU2YjAwMDg5YzYzN2FjNSx2TExVYXZPRw%3D%3D&b=t%3AuNoi0AujsProexVbD5JsWA&p=http%3A%2F%2Fthranduilsperkybutt.tumblr.com%2Fpost%2F178421504186%2Fwarnings-nsfw-grace-kink-gif-source-gadreel&m=0)

> _Imagine Gadreel making you cum by using his grace while you are trying to have a conversation with his brother, Gabriel._

———  _Request for anon_  ———

“… and that’s the only explanation, right?”

God, you really wished you could concentrate on a word Gabriel was saying right now. You shift in your seat, hoping you don’t look too obviously uncomfortable as you let out a slow sigh in an attempt to cool your body down in vain.

“Yeah.”

“Exactly! And…”

Gabe’s words zone out of your attention as you spare a directed glare at Gadreel, who seemed utterly innocent at the head of the library’s table, as if he wasn’t even paying the least bit of attention to the two of you. You know better than that, though, because for the past five minutes, he had been roaming your body with his grace. The feeling had been light at first, like a warm caress every now and again, but his intent soon became clear as he pressed and prodded the most intimate parts of your body, clearly toying with you in the most mischievous of ways. If you didn’t know better, you’d say he was a demon for how much pleasure he got from messing with you like this.

You find yourself nearly gasping aloud, barely able to contain the noise into a small squeak as his grace delves between your thighs once again, paying direct attention to you in just the way he knows drives you crazy.

“Are you alright?” Gabriel manages, breaking the conversation to raise a brow at you across the table.

You swallow thickly, steeling yourself as Gadreel’s grace gets even more intense, clearly testing your ability to stay quiet, “Uh, yeah, just had a hiccup, there.”

When you glance back to Gadreel, you silently curse the smirk you see along his lips.


	2. Benny Lafitte, Dean Winchester - being in a polyamorous relationship with Benny and Dean and them tag-teaming you all night long on your birthday.

_**** _

_**** _

_**Warnings:** NSFW_

Gif source:  [Here](https://t.umblr.com/redirect?z=http%3A%2F%2Frebloggy.com%2Fpost%2Fspoilers-supernatural-dean-winchester-jensen-ackles-mystuff-gifs-supernatural-be%2F37310758703&t=NmQxYmNhYjUwMWE5ODVmZmU2OTA1NWU2ZjE0Y2QyNmE3YmFjYThhOCw4QWtHMGJBUQ%3D%3D&b=t%3AuNoi0AujsProexVbD5JsWA&p=http%3A%2F%2Fthranduilsperkybutt.tumblr.com%2Fpost%2F178399518528%2Fwarnings-nsfw-gif-source-here-imagine-being-in&m=0)

> _Imagine being in a polyamorous relationship with Benny and Dean and them tag-teaming you all night long on your birthday._

———  _Request for anon_  ———

“Don’t tell me you’re worn out already?” Dean chuckles as you take a moment on the bed, gasping from the high of the orgasm you’d just been on the receiving end of thanks to Benny, who seemed rather pleased with himself as he sits up on the bed.

Dean was already halfway on top of you by the time you manage an answer, “You wish, Winchester. I can take whatever you boys can give.”

“I’m gonna’ hold you to that, baby,” Dean hums before his lips come crashing down to yours in a searing kiss that nearly takes your breath all over again.

As Dean completely dominates your senses, you hear Benny beside you hum his agreement, “We’re gonna’ take real good care of our birthday girl tonight. That was just round one, darlin’.”


	3. Dean Winchester - Dean catching you masturbating and moaning his name.

_**Warnings:**  NSFW_

Gif source:  [Dean](https://t.umblr.com/redirect?z=https%3A%2F%2Fgfycat.com%2Fgifs%2Fdetail%2FInferiorQuarrelsomeIsabellineshrike&t=YjlmNTM2MmNkZTc1N2EzNmVjZTY0YjQwMjIzOTY2Yzk5ZTMyNDE3OSw1d3VLZk51NA%3D%3D&b=t%3AuNoi0AujsProexVbD5JsWA&p=http%3A%2F%2Fthranduilsperkybutt.tumblr.com%2Fpost%2F176563695838%2Fwarnings-nsfw-gif-source-dean-imagine-dean&m=0)

> _Imagine Dean catching you masturbating and moaning his name._

———  _Request for anon_  ———

Dean was rubbing his neck, certain the long drive back to Kansas had resulted in a cramp there, but at least they’d made it home early thanks to his reluctance to take a break from the drive. His own bed was calling to him; that memory foam mattress was about to get real familiar with his body as he slept off the worries of the hunt.

He passes by your room on the way to his own, noticing the door was cracked, but the pitch black darkness within lures him to believe you’d already gone to bed by now. He wasn’t really surprised, it was quite late.

Dean had nearly passed the room when a low, breathy groan hits his ears. Stopping in his tracks, Dean turns towards the door, listening acutely for anther sound. He doesn’t have to wait long, another gasp accompanied by the distinct sound of a moan that sets him on edge.

His body moves of its own accord, taking him silently towards the door. He knew better than this, but the sounds you were making went directly to his groin. Sleep was the last thing on his mind.

Dean’s forehead hits against the wall quietly as he listens to the sounds of you getting yourself off, feeling dirty for listening in, but not guilty enough to leave. Dean swallows thickly, trying his best to keep from palming himself through his jeans, but his inhibitions completely sever at one final sound.

It was quiet, breathy, and far more erotic than he’d ever thought was possible as he heard you elongate a name in a moan, “Dean… Oh, Dean…”


	4. Castiel - you and Castiel have danced around your feelings for each other for the longest time and it finally coming to a head one weekend that Sam and Dean aren’t in the bunker and you decide to spend the entire time teasing the poor angel until...

_**Warnings:**  NSFW_

Gif source:  [Castiel](https://megmeg-chan.tumblr.com/post/173983905432/magnificent-winged-beast-good-intentions-spn)

> _Imagine you and Castiel have danced around your feelings for each other for the longest time and it finally coming to a head one weekend that Sam and Dean aren’t in the bunker and you decide to spend the entire time teasing the poor angel until he can’t take it anymore._

———  _Request for anon_  ———

The gloves were off. You were doing everything you could to finally get Castiel to snap like a twig. At the start, your feelings for him had been cautious and sweet, shooting electric excitement through you whenever he was around. Last week you’d come so close to breaking through the eternal friendship that surrounded the two of you— the hunt had thrown you both into a heated situation, and you’d never forget the way he looked at you when you made it through— only for him to back off entirely from taking the leap.

With the Winchesters out of town, you were taking full advantage of the empty bunker and unsuspecting angel within. You weren’t going to hold back anymore.

Suddenly all your outfits were a little skimpier, a little tighter in all the right place, your gaze lingered on his in a more seductive way than it usually did, and you knew it was getting to him. You could feel Castiel’s eyes trail after you, his cheeks flushing whenever you flirted with him.

And then you came right on into the library to find him pouring over some ancient tablet, only for you to sit right into his lap with a simple question of, “What’s this?”

Castiel clears his throat, his hands gripping the arms of the chair to keep from grabbing you, “Uh, Dean called about it. He wanted me to take a look.”

“Oh,” you hum, glancing back towards him to catch the look of suspicion in his eye before you give a nod and hop back up, satisfied with how quickly he shifts his weight in the chair, “well, I’m gonna’ go to bed.”

You make it to your room for about five minutes before you hear his presence in the doorway, his hands settled on either side of the frame as he somewhat glares at you, voice gruff as he asks, “What are you doing?”

“Uh, getting ready for bed?”

“No,” you’re shocked with how few steps it takes for him to advance upon you, standing far too close far too quickly as he looks at you in a way that you’d been craving for months. Castiel tilts his head at you, demanding and direct, “You have to be aware of what you’ve been doing. You are trying to seduce me.”

You can’t help but smirk up at him, “Has it been working?”


	5. Benny Lafitte, Dean Winchester - having a threesome with Benny and Dean.

_**Warnings:** NSFW_

Gif source:  [Here](https://t.umblr.com/redirect?z=http%3A%2F%2Frebloggy.com%2Fpost%2Fgifs-supernatural-dean-winchester-jensen-ackles-alec-dark-angel-ty-olsson-benny%2F40887095916&t=NGQ3ZDdiYTBiMzQ2MWQ3ZDk5ZGNiY2Q0YjEyYTczZDVlMWM5OTcwNSw4YjhUMVJCSw%3D%3D&b=t%3AuNoi0AujsProexVbD5JsWA&p=http%3A%2F%2Fthranduilsperkybutt.tumblr.com%2Fpost%2F175935081033%2Fwarnings-nsfw-gif-source-here-imagine-having-a&m=0)

> _Imagine having a threesome with Benny and Dean.  
> _

———  _Request for anon_  ———

There was something about the bayou. Some otherworldly quality that made you lose your sense of time and direction, drawing all kinds of creatures to it that didn’t end with the gators. This past week spent hunting a nest of vampires with Benny and Dean— in that time the bayou had seeped into every part of your body. Sweat and dirt and swamp water soaked your bones, it felt like. Exhaustion rolled through you like a wave, and you weren’t sure if you were eager or reluctant to leave the area when the last head rolled from the last vampire’s shoulders.

You were all wound up when you made it back to the motel.

A week’s worth of that Cajun accent still didn’t make you immune to the hot shiver Benny’s call of, “Darlin’,” sent through you.

Dean’s eyes darted between the two of you as he wiped the dirt and blood from his fingers, an almost desperate, “I’m gonna’ hit the shower. I need a good scrubdown,” coming from the hunter in an effort to escape the tension that had come to surround the three of you. You were fighting a losing battle by now, the tension had already wore you down to your raw center, threatening to result in the kind of night that you’d only ever imagined in the privacy of your darkest fantasies.

When his boots hit the tile of the open bath, his hand gripping the door as he pushes it open, you don’t let him escape that easily.

Finally, you bring the topic the three of you have all been dancing around to a head with a deep sigh and declaration of, “I need a good fuck.”

 

 


	6. Sam & Dean Winchester - making a sex tape with Sam and Dean Winchester.

**Summary for the Chapter:**

> **Warnings: NSFW, Incest**

_**Warnings:** NSFW_

Gif source:  [Here](https://megmeg-chan.tumblr.com/post/169298095512/cinemaspam-my-mouths-itchy-is-that-normal)

> _Imagine making a sex tape with Sam and Dean Winchester._

———  _Request for anon_ ———

“Well, what’d she say?” Sam prompts as Dean sits on the edge of the motel bed, consumed with whatever text he was in the process of typing.

“Oh, she’s in,” Dean’s grin only widens slightly when he emphasizes, “So in.” When he finally does look up to see Sam, there’s an excited glisten in his eyes, one that Sam could only compare to a kid in a candy store, “You’ve got five minutes to get that camera set up before she gets here.”

 

 


	7. Benny Lafitte - after a night together, having to sneak Benny out of your room before Dean and Sam wake up.

Gif source:  [Benny](https://megmeg-chan.tumblr.com/post/150256645242)

> _Imagine, after a night together, having to sneak Benny out of your room before Dean and Sam wake up._

———  _Request for anon_  ———

“Darlin’, if I didn’t know better—”

“Shhh!” you giggle, clasping your hand around Benny’s grin only for him to pull it down and whisper back at you from beneath the motel doorway.

“If I didn’t know better, I’d say you were in a hurry to get rid of me.”

“Do you want them to wake up?” he rolls his eyes at that, pacified by your lips pressing against his one last time for the night— well, morning at this point.

“Hell, let ‘em hear,” he hums before you give him one last half-hearted shove out the door. Benny tips his hat to you, shooting a grin when you bite your own, “I’ll see you later, darlin’.”

 

 


	8. Sam & Dean Winchester - Sam and Dean seeing you in a dress for the first time and both of them can’t wait to get back to the motel and you out of the dress.

Gif source:  [Here](https://megmeg-chan.tumblr.com/post/134668720097/out-in-the-open-i-think-ill-call-them-the-fbi)

> _Imagine Sam and Dean seeing you in a dress for the first time and both of them can’t wait to get back to the motel and you out of the dress._

———  _Request for anon_  ———

“Okay, let’s go.” Sam and Dean turn towards you in unison, catching the sight of you in the dress you decided to wear. You glance between them quickly, noticing their stares, “What?”

Dean turns his head back towards the impala, but not before you catch the pink tinge on his cheeks as he clears his throat, “Let’s just get tonight over with.”

As you make to move past Sam in your path to the back seat of the impala, he grasps you by your elbow and pulls your close enough that he can keep his voice low in your ear, “You look  _amazing_.”


	9. Dean Winchester - you and Dean trying out ice play.

_**Warnings:** NSFW_

Gif source:  (( _Unknown_ ))

> _Imagine you and Dean trying out ice play._

———  _Request for anon_  ———

He knew you wanted to spice things up in the bedroom, but when you pulled out the ice bucket, he couldn’t keep his surprise from appearing all over his face. Dean’s naturally perfect eyebrows shoot up at you, lips turning just slightly to let you know he wasn’t completely opposed to the idea, should you explain yourself.

“Ice?” Dean asks as you place a small cube in your mouth, grinning around it as you bring your lips closer to his.

He gets the idea when you hum an answering, “mhm,” as you slip the cube down to his own mouth, letting him taste the cold water as it melts on his tongue. Your combined tongues around the ice melts it all faster than he’d expected, dissolving into a heated kiss that had hardly been cooled at all by it.

“What do you think?” you ask, just barely breathless in the wake of your kiss.

“I think this is a great idea.”


	10. Crowley - having shower sex with Crowley.

_**Warnings:** NSFW_

Gif source:  [Crowley](https://megmeg-chan.tumblr.com/post/169300464937)

> _Imagine having shower sex with Crowley._

———  _Request for anon_ ———

Your hand slaps against the wall, a smack resounding throughout the bathroom in your desperate attempt to ground yourself despite the hold the man against you had on your thighs. Crowley chuckles low, amusement lighting his eyes for a flicker of a moment before they return to their lecherous observation of your naked body.

“Scared you’ll slip, darling?” his tease only further reminds you that he was, in fact, a demon, because it was in far too much mirth at your brief moment fear when he’d shifted your weight more thoroughly against him. If he wanted, he could drop you, and if you didn’t know him as well as you did, you wouldn’t know why you trusted him with this.

“Oh, shut up,” you shoot him a glare that wasn’t fully committed in it’s spite, reaching to wrap your arm around his neck as his lips crash against yours and press you further into the shower wall.

Between this kiss and the next, Crowley murmurs, “I won’t let you fall.”


	11. Sam & Dean Winchester - getting snowed in with Sam and Dean and finding a sexy way to keep warm.

_**Warnings:** NSFW_

Gif source:  [Here](https://megmeg-chan.tumblr.com/post/141811250882/saucynewf-ghostfacers-313-for)

> _Imagine getting snowed in with Sam and Dean and finding a sexy way to keep warm._

———  _Request for anon_  ———

The weatherman had predicted it would snow, but definitely not this much. The hunt was officially on hold thanks to the sheer amount of snow that covered every exposed surface outside, forcing you to be cooped up in a cabin that was definitely not equipped with a heater strong enough for this weather. It was trying it’s best, whirring loudly near the single window of the room, but hardly heated the whole place as much as you wanted. Luckily, there was a small fireplace, but even that reached only far enough for you to have to huddle around it, flanked on each side by the flannel-clad Winchester men.

“It would have to freeze over in the middle of the night,” Dean bitterly comments, warming his hands in front of the fire as you return with a large blanket you’d snatched off of one of the beds.

“It’s cold as balls in here,” your correction gets a chuckle from Sam, who gladly joins you in wrapping the blanket around your shoulders when you offer.

“Now you’re starting to sound like Bobby,” his joke makes it easier for you to pretend that you weren’t pressed as close to the younger Winchester as you were.

Instead, you give your attention to Dean, who was now hopelessly trying to poke the fire to go hotter, “Dean, why don’t you just get under the blanket with us? It’s not gonna’ get any warmer in here.”

He sighs, abandoning the poker in it’s stand, “Don’t have to tell me twice.” Kicking off his boots, he moves towards the two of you, snuggling into your side as he pulls the blanket around his shoulders as well.

“Watch your hands, Winchester,” you huff, unable to stop your blush this time when Dean grazes your boob on accident.

Suddenly, the whole mood shifts when Dean’s teasing smirk appears, “You wish, sweetheart,” and you snort in return.

Before you think, you’re teasing him right back with your own sarcastic, “Oh, like you boys aren’t itching to play a little grab-ass with me.”

Sam laughs beside you and suddenly you find yourself a little too close to both of them as they lean a little closer when he hums, half-playful, half-serious, “Are you suggesting a different way of keeping warm?”


	12. Sam & Dean Winchester - Sam and Dean questioning you about any fantasies you want to try out with them and you being embarrassed to admit you want to try pegging.

_**Warnings:** NSFW; Pegging_

Gif source:  [Here](https://megmeg-chan.tumblr.com/post/153336839982/devoiddean-celebrating-the-life-of-asa-fox)

> _Imagine Sam and Dean questioning you about any fantasies you want to try out with them and you being embarrassed to admit you want to try pegging._

——— _Request for anon_  ———

“What’s that look for? It can’t be that bad,” Dean teases, pointing out the embarrassment written across your face. It only serves to make you feel even more in the spotlight until he jokes, smirking behind his drink as he takes another sip, “Definitely not as kinky as Sam’s was.”

Sam purses his lips at Dean in annoyance before rolling his eyes, apparently deciding not to get into it right now, “Really, we want to know. I mean, you know ours. It’s only fair.”

“It’s just,” you begin, suddenly immensely interested in the lines of your palm as you avoid their eyes, “I don’t know if you would be into it.” You were sure you were sweating with the heat that they’d brought to your face with their constant questioning. Forming what you wanted into words had never been your strong suit, and certainly not when it came to your fantasies in the bedroom.

Sam pulls you away from your internal conflict when he reminds, “You’ll never know if you don’t tell.”


	13. Crowley - convincing you to make a sex tape with him.

_**Warnings:** NSFW_

Gif source:  [Crowley](https://megmeg-chan.tumblr.com/post/158052898642/bookwormirmak-me-about-everything)

> _Imagine Crowley convincing you to make a sex tape with him._

———  _Request for anon_ ———

“Darling, you would look wonderful in front of a camera,” Crowley tries, yet again, to tempt you into making a tape with him. He’d gotten this great idea a week ago and hadn’t stopped suggesting it since.

You, however, weren’t so sure about it. You were hardly able to take a selfie you liked, let alone be comfortable with making a sex tape! The mere idea of yourself, naked on camera was enough to give you anxiety. What if you looked utterly horrible when filmed? Or worse, what if someone besides just the two of you saw it?

But, the more he talked about it, the more enticing the idea sounded. You’d gone from a hard no to straddling the fence on your resolve. Maybe it kind of turned you on, too, to think about rewatching all the things he did to you and noticing the parts of his reactions that you’d missed while in the moment.

You sigh, looking at Crowley with a blush that spoke far more than you let on as you told him, “Let me think about it, okay?”


	14. Dean Winchester - being Dean’s younger sister and Sam’s older sister and being Dean’s soft Dom.

**Summary for the Chapter:**

> **Warnings: NSFW; BDSM subDom relationship; Incest; A single F bomb; Also, my possible poor writing of subDom dynamics**

_**Warnings:** NSFW; BDSM subDom relationship; Incest; A single F bomb; Also, my possible poor writing of subDom dynamics_

Gif source:  [Dean](https://megmeg-chan.tumblr.com/post/162790066842/frozen-delight-spn-parallels-dean-packing)

> _Imagine being Dean’s younger sister and Sam’s older sister and being Dean’s soft Dom._

———  _Request for anon_  ———

There was always a nagging feeling in the back of your mind when you were keeping something from your brothers, but this— this was too big of a secret to let Sam in on. Both you and Dean were keenly aware of just how fucked up this thing was that had started between you, but that didn’t stop either of you from sharing a knowing glance when Sam had offered to go and grab dinner.

Before Sam can hop in the impala, it starts, going completely over his head when you hum at Dean, “Dean, go and grab my bag out of the impala before Sam leaves.”

Dean clears his throat, nodding before heading out the door after Sam with such a casual, “Yes, ma’am,” that it didn’t even sound out of place. Excitement sparks within you and by the time he returns with your duffel in hand, the rev of the impala as Sam pulled off barely registering in your ears, you’ve already shifted into your Domme state-of-mind. Dean watches you after he closes the door, waiting for the command he knows is coming. You let him stand there for a moment too long as you close your laptop and set it aside, finally giving him the attention of your eyes and noticing how his tongue darts out to wet his lips in anticipation.

“Do you want to know what will make me happy, Dean?”

“Yes,” he says, pausing before he realizes what is supposed to come after it, “please.”

“We’ve been hunting all day and I’m tense. In my bag you’ll find my lotion,” you stretch for emphasis, unable to stop your smirk at how he was trying to be obediently submissive since you’d ignored giving him this for the last day and a half. “Come over here; you’re giving me a massage.”


	15. Dean Winchester & Endverse!Dean - being Dean’s girlfriend and you both get sent to endverse!2014 and you convince Dean and 2014!Dean to have a threesome. That way you can have the threesome you’ve fantasized about and Dean can’t really get jealous...

_**Warnings:**  NSFW_

Gif source:  [Here](https://megmeg-chan.tumblr.com/post/167568002542/mishacolins-504-622-1304)

> _Imagine being Dean’s girlfriend and you both get sent to endverse!2014 and you convince Dean and 2014!Dean to have a threesome. That way you can have the threesome you’ve fantasized about and Dean can’t really get jealous about you having sex with a different guy._

———  _Request for anon_ ———

“You want to  _what?_ ” Dean from the future had the same shocked expression your Dean had, the two of them looking at you as if you’d just grown another head. It was trippy, hearing the two of them call out in unison, but you were far from the kind of person to not take full advantage of having two Dean Winchesters standing in front of you.

“You heard me,” you shoot back, moving towards the two identical men with seductive purpose until you stand directly in front of the 2014 version of Dean, smoothing your hand along his military jacket before you hit him with the same puppy eyes that worked on your Dean, “Come on. There’s no room for jealousy when it’s still you, right, Dean?”

“I remember that look,” Dean hums down at you in an almost sad way and, for a moment, the question of your future whereabouts cross your mind before you realize you didn’t want to know the answer. You move away from him and back to the side of your Dean, hitting him with the same look as you tug him towards you by your grip on his blue collar.

“What do you say, Dean?”


	16. Crowley - the heat going out in your room and instead of snapping his fingers to fix the heat, your boyfriend, Crowley decides he’d rather ‘keep you warm’ all night long.

Gif source:  [Crowley](https://megmeg-chan.tumblr.com/post/167567873092/dean-winchester-crush-we-always-do)

> _Imagine the heat going out in your room and instead of snapping his fingers to fix the heat, your boyfriend, Crowley decides he’d rather ‘keep you warm’ all night long._

———  _Request for anon_  ———

Crowley appears behind you with a cocky smirk, causing you to have to turn in order to see him, “To what do I owe the pleasure, love? You miss me?” When he sees the deadpan expression in your eyes and takes in your appearance— a sweater with a blanket wrapped around your shoulders— he nods, “Ah, so the unbearable cold is not by choice, I assume?”

“When hell freezes over,” you manage the joke, getting a roll of his eyes in return. “Look, if you could just fix the heat all snappy-snappy,” you snap your fingers for emphasis, “that would be great. I really don’t want to have to pay to get it fixed in the morning and suffer all night until then.”

Crowley takes a step towards you, smirk widening, “Oh, but why do that when I can think of a way to keep you warm that’s much more fun?”


	17. John Winchester - having make-up sex with John Winchester after an argument.

_**Warnings:** NSFW_

Gif source:  [John](https://megmeg-chan.tumblr.com/post/165474223672/greensarrow-jeffrey-dean-morgan-as-brian)

> _Imagine having make-up sex with John Winchester after an argument._

——— _Request for anon_  ———

“What are you pulling over for?” you huff as the car swerves on the highway, slowing to a stop on the side of the road. You look towards John, who had had you fuming since you got into the car twenty miles back.

“Oh, she speaks,” John responds sarcastically, annoyance etched into his features and causing you to look back indignantly towards the pines to your left. “Listen here, if you think you’re going to go all the way to town ignoring me because of what happened back there, and that I’m going to put up with it, you’re outta’ your mind.”

“You want me to talk, John?” you snap back, fixing him with a fiery look that was a product of the argument at hand, “Fine, I’ll talk. I’ll tell you all about how shitty it was of you to—” 

He silences you with a grip to your arm, pulling you the short ways along that seat of the impala towards him, his lips pressing against your own mid-sentence. You push him back instinctively and he easily moves at your shove, though you find yourself pulling him back just as aggressively. You were so pissed off at him, but you didn’t want to go all the way back to town in dead-silence either, in all honesty.

“I’m still mad at you, Winchester,” you growl against him and get a hinted glare in return as his lips trail along your jaw. John shifts in the seat to push you down against it.

“Good, ‘cause I’m still mad at you, too, darlin’.”


	18. John Winchester, Negan - having a threesome with Negan and John Winchester.

**Summary for the Chapter:**

> **Crossover: Supernatural & The Walking Dead**

_**Warnings:** NSFW; AU-ish_

Gif source:  [Negan](https://megmeg-chan.tumblr.com/post/153000777442/richonnebitch-negan-2)  |  [John](https://megmeg-chan.tumblr.com/post/151599525732)

> _Imagine having a threesome with Negan and John Winchester._

———  _Request for anon_  ———

“C’mere,” Negan smirks from where he sits on the bed, utter amusement radiating off of him as he watches a similar looking man to himself kiss down your neck from behind. You ache to move towards him, arching in John’s grip, but don’t dare break from John’s hold. You were torn, in those few seconds.

Luckily, you don’t have to choose.

John pushes you forward with a demanding urge of, “Go on, darlin’,” near your ear, keeping a grip on your waist when your back parts from his chest obediently. That small gap is closed just as quickly as it appears as soon as you stop in front of Negan, John’s presence staying close as Negan pulls you to straddle him before eagerly capturing your mouth with his own. He was far more openly excited about the situation you found yourselves in than John was, though you weren’t in doubt that John was enjoying himself, too. They just showed their enthusiasm differently.

While John’s fingers move against the bondage of your underwear which were soon to be gone, Negan breaks to chuckle briefly against your lips after you moan into him, “Are you fuckin’ enjoying yourself, sugar?”


	19. Dean Winchester - Imagine Dean being a sub to you. (Gender neutral reader requested)

**Summary for the Chapter:**

> **Warnings: NSFW; subDom**

_**Warnings:** NSFW; subDom_

Gif source:  [Dean](http://megmeg-chan.tumblr.com/post/161720554092)

> _Imagine Dean being a sub to you. (Gender neutral reader requested)_

———  _Request for anon_  ———

“My safe word’s ‘apple pie,’” Dean had stated the first time you’d done this. As of yet, he’d never had to use it. You hadn’t gone too far as his Dom, wanting to ease into the relationship slowly before you really tested him.

But now you were ready to test him.

That’s why, as soon as Dean had walked into the motel room, you’d pushed him against the door and ordered, “Tell me your safe word.”

It obediently came from Dean, “Apple pie.”

“You use it if I go too far tonight, okay?”

“Okay.”

“Now,” you sigh, leaning away from him but letting your hand linger as it smoothed down his chest before finally moving away from his reach, “I want you naked on the bed when I get out of the bathroom. Can you be good and do that for me, Dean?”

Dean wets his lips with his tongue, nodding as he glances towards the bed, already unbuttoning his shirt for you, “Hell yeah I can.”


	20. Dean Winchester - Dean putting a vibrating dildo inside you and using it on you while you eat dinner with Sam and Cas. However, Dean gets distracted by pie and ups the vibration, making you orgasm in front of Sam and Cas.

_**Warnings:**  NSFW_

Gif source:  [Here](http://megmeg-chan.tumblr.com/post/150948726922)

> _Imagine Dean putting a vibrating dildo inside you and using it on you while you eat dinner with Sam and Cas. However, Dean gets distracted by pie and ups the vibration, making you orgasm in front of Sam and Cas._

———  _Request for anon_  ———

You were staring down at your half-eaten meal, thanking your lucky stars that Sam and Cas were preoccupied with Dean at the moment as he gushed over his pie. You were dying, trying your hardest to not let the increased vibration take you over the edge.

Why did you ever let Dean talk you into this?


	21. John Winchester - John patching you up after you get injured during a hunt and you keep kissing him and trying to seduce him. He’s reluctant at first, because he doesn’t want to re-open your wounds, but finally he gives in and the two of you end up...

_**Warning:** NSFW_

Gif source:  [John](http://megmeg-chan.tumblr.com/post/154775677997)

> _Imagine John patching you up after you get injured during a hunt and you keep kissing him and trying to seduce him. He’s reluctant at first, because he doesn’t want to re-open your wounds, but finally he gives in and the two of you end up having careful sex._

———  _Request for anon_  ———

When your lips part from his, John smiles, “That’s a hell of a thank you.”

“I’m not done, yet,” you smirk, trailing your lips along his jaw, his stubble scratching you.

“You shouldn’t work too hard after the beating you took on the hunt tonight,” John warns, hands reflexively going to your hips as you press him back on the motel bed, the first aid kit beside you a reminder that he’d just gotten done patching you up.

“We’ll just have to go slow, then.”


	22. Dean Winchester - Sam not getting any sleep because you and Dean were having sex and being too loud in the next room and the next morning Sam says that Dean has corrupted you because you used to be so shy and quiet.

_**Warnings:**  NSFW_

Gif source:  [Here](http://megmeg-chan.tumblr.com/post/153336839982/devoiddean-celebrating-the-life-of-asa-fox)

> _Imagine Sam not getting any sleep because you and Dean were having sex and being too loud in the next room and the next morning Sam says that Dean has corrupted you because you used to be so shy and quiet._

———  _Request for anon_  ———

“Sleep well?” Dean asks as he walks into the kitchen to find Sam nursing a coffee, dark circles under his eyes. The eldest Winchester looks quite the opposite, a bit of a skip in his step seeing as his night had gone very well.

“No, thanks to you and (Y/N),” Sam huffs half-heartedly, far too tired to be angry at the moment.

“Well, what can I say?” Dean chuckles, pouring himself a coffee, “She’s wild in the sack.”

“I blame you for corrupting her, Dean,” Sam accuses with a roll of his eyes and a sigh, “She used to be all shy and quiet.”


	23. Balthazar - being a tease whilst eating you out.

_**Warnings:**  NSFW_

Gif source:  (( _Unknown_ ))

> _Imagine Balthazar being a tease whilst eating you out._

———  _Request for anon_  ———

“What’s that, love?” he leans away from you, making you groan louder as you glare down to meet his grin.

“You’re such a tease,” you accuse, shifting your hips towards him in a silent plea for him to touch you again.

Dipping his head back down, he chuckles against the flesh of your thigh, “That I am.”


	24. Sam Winchester - Sam teasing you about how tired out you are after sex with him.

_**Warnings:**  NSFW_

Gif source:  [Sam](http://megmeg-chan.tumblr.com/post/131318989532)

> _Imagine Sam teasing you about how tired out you are after sex with him._

———  _Request for anon_  ———

“Ugh,” you groan as you throw your duffel in the back of the impala, glancing up at the motel as Sam shuts the trunk for you, “I need a coffee.”

“Worn out after last night, huh?” Sam teases, causing a blush to spread on your face along with a knowing smirk.

“Well, I was kept up until three in the morning despite the fact that we had to get up at five,” you hum back, shooting him a flirtatious look that has him letting out a chuckle as he shrugs.

“Ah, well, the least I can do, since it’s my fault, is to get you a coffee,” Sam smirks, and the two of you are snapped from your flirting as Dean returns from the motel’s office, having given the room key back to the front desk.

“What do you guys want for breakfast?” Dean asks as you all pile into the impala.

Sam glances at you in the back seat, still smirking, “Somewhere we can get a coffee.”

Dean nods sleepily in agreement, not catching the unspoken between you and Sam, “I hear that!“


	25. Castiel, Gadreel - licking up Gadreel’s length and slowly making him twitch and beg while gripping the chair he’s in, and only swallowing him down when Castiel comes in, startling them both.

_**Warnings:**  NSFW_

Gif source:  [Gadreel](http://megmeg-chan.tumblr.com/post/159126723397)  |  [Castiel](https://t.umblr.com/redirect?z=http%3A%2F%2Fanqel.co.vu%2Fpost%2F148755404024&t=YmZkNzBmNTQ1M2M4ZTMyOTc4ZmRiZjZkMzBmYmU2YjZjNDY0MTY5NixQbnh4ZGJ6ag%3D%3D&b=t%3AuNoi0AujsProexVbD5JsWA&p=https%3A%2F%2Fthranduilsperkybutt.tumblr.com%2Fpost%2F160450640904%2Fwarnings-nsfw-gif-source-gadreel-castiel&m=0)

> _Imagine licking up Gadreel’s length and slowly making him twitch and beg while gripping the chair he’s in, and only swallowing him down when Castiel comes in, startling them both._

———  _Request for anon_  ———

You already had Gadreel on the edge, needing just the final push you weren’t giving him to fall off into his own orgasm. You wanted to draw it out, make him squirm and beg in his seat, and you were succeeding. He gripped the armrests of the chair for dear life, it seemed, as you drew moans and gasps from his throat.

As the door behind him opens, revealing Castiel, you lock eyes with the startled angel before taking Gadreel all the way down, swallowing around him as you decide now is the perfect time to bring him to a finish.

By the time you pull away, Gadreel’s length falling from your mouth with a pop, your smirk widens at the sight of them. Gadreel was panting, breathless and far too spent to worry for Castiel standing in the doorway. Castiel, on the other hand, held a deep crimson blush that slowly crept up his neck, his eyes watching a bit too long before he finally averts them, attempting an apology at his intrusion.

With a single sentence, you calm his nerves, “Don’t apologize, Cas.”


	26. Gadreel - wanting Gadreel to spank you and having to explain to him that it turns you on.

**Summary for the Chapter:**

> **Warnings: NSFW; Spanking**

_**Warnings:** NSFW_

Gif source:  [Gadreel](http://megmeg-chan.tumblr.com/post/142139152217/drawsshits-the-shirtless-tahmoh-gifs-that-i)

 

> _Imagine wanting Gadreel to spank you and having to explain to him that it turns you on._

———  _Request for anon_ ———

“Spank me?”

“Why would you want me to cause you physical pain?” Gadreel asks, his brows furrowed in genuine confusion at the request you’d whispered in his ear.

“Sometimes it’s nice to mix a little bit of pain with pleasure, Gadreel. It turns me on.”


	27. Sam & Dean Winchester - skinny dipping with the Winchesters on a hot summer night.

_**Warnings:** NSFW_

Gif source:  [Winchesters](http://megmeg-chan.tumblr.com/post/142729762312/stonenumberone-love-is-1)

> _Imagine skinny dipping with the Winchesters on a hot summer night._

———  _Request for anon_  ———

You couldn’t bring yourself to particularly care about what part of Arizona you were in as Dean drove the three of you towards Alabama. At least until he had pulled off the road in the middle of nowhere for a break. The two Winchesters were looking up at the stars on the bank of this lake you’d managed to find, but your eyes were focused on the water. The summer heat of the day hadn’t quite dissipated under the night sky, making the lake look more and more inviting with every second that passed.

That was why you got up and started stripping off your shirt, “I’m going for a swim.”

Dean looks towards you with a scoff, “You didn’t bring your swimsuit with us.”

With a smirk, you ask him as you strip out of your pants, “Who needs a swimsuit?”

Sam’s eyes go wide as you head towards the water, “Are you gonna’ swim in your underwear?”

Hooking your thumbs in the hip of your panties, you call, “Nope!” You don’t see the stunned looks on their faces as you strip all the way before diving in, and by the time you come up for air they’re heading towards the lake, too, each stripping down. “You boys deciding to cool off, too?”


	28. Gadreel - playfully smacking Gadreel’s butt after a hunt and it really turns him on.

Gif source:  [Gadreel](http://megmeg-chan.tumblr.com/post/142139052852/nicoleanell-favorite-battlestar-galactica)

> _Imagine playfully smacking Gadreel’s butt after a hunt and it really turns him on._

———  _Request for anon_  ———

He turns around with a shocked look on his face, catching your mischievous grin as you let out a chuckle. Trekking through these woods for the hunt was more entertaining than you’d thought it would be with him walking in front of you. How could you not tease him by smacking his butt?

Gadreel’s shock turns to lusty amusement in a matter of milliseconds as he playfully chastises, “We are on a hunt, and you intend to distract me?”


	29. John Winchester - sex with John Winchester to the song ‘You Can Be The Boss’ by Lana Del Rey.

_**Warnings:** NSFW_

Gif source:  [John](http://ahhhgifhunts.tumblr.com/post/42120142248/jeffrey-dean-morgan-gif-hunt)

> _Imagine sex with John Winchester to the song ‘You Can Be The Boss’ by Lana Del Rey._

———  _Request for gabby227_  ———

_You taste like the Fourth of July  
Malt liquor on your breath, my, my…_

Music wafted from the desk of the motel room where your phone sat, discarded, abandoned just as it had been before he’d interrupted you. The playlist had gone through a few songs by now, unhindered, thanks to John’s distraction.

You could taste the bar on him; he’d been drinking. His skin hot from both the rush of alcohol and the sweat that he’d worked up on top of you. John’s hands on your wrists push them into the pillows behind your head as his lips nip at the pulse of your neck, letting you know he was in the mood that would leave you under his control tonight.

Not that you minded at all.

_You can be the boss, daddy_  
You can be the boss  
Taste like a keg party, back on the sauce  
I like you a lot, I like you a lot  
Don’t let it stop…


	30. Dean Winchester - walking in on Dean while he’s sounding and staying to watch.

_**Warnings:** NSFW_

Gif source:  [Dean](http://megmeg-chan.tumblr.com/post/137063899092/im-just-sayingi-think-a-smut-apocalypse-would)

> _Imagine walking in on Dean while he’s sounding and staying to watch._

———  _Request for anon_  ———

“I’m sorry,” was already on your lips as soon as you realized what you’d walked in on, but it dies in your throat as soon as you lock eyes with Dean.

He lets out an involuntary moan, eyes intense as they look at you through their lust, “Close the door.”


	31. John Winchester, Rafael Barba - having a threesome with Rafael Barba and John Winchester.

**Summary for the Chapter:**

> **Crossover: SPN & Law and Order: SVU**

_**Warnings:** NSFW_

Gif source:  [John](http://megmeg-chan.tumblr.com/post/150954194657)  |  Barba ((Unknown))

> _Imagine having a threesome with Rafael Barba and John Winchester._

———  _Request for anon_  ———

You had hit the jackpot at that bar, flanked by two men who each were determined to be the one to take you home. For the last two hours, you’d been enjoying their attempts at flirting with you, as well as their conversation. In that time, you’d learned one had grown up in the Bronx and the other spent his life on the road.

“Well, John, Rafael,” you sigh as you down the last bit of your drink, a smirk dancing on your face as you decide to level them with your proposal, “I think it’s time to go home.” You relish in the brief disappointment that flashes along their faces before you continue, “So, which one of our places should we go to?”


	32. Dean Winchester - Dean having a mommy kink.

**Summary for the Chapter:**

> **Warnings: NSFW; Mommy kink**

_**Warnings:** NSFW; Mommy kink_

Gif source:  [Dean](http://megmeg-chan.tumblr.com/post/137063899092/im-just-sayingi-think-a-smut-apocalypse-would)

> _Imagine Dean having a mommy kink._

———  _Request for anon_  ———

You were both close, but Dean was wearing his desperation on his sleeve. His brow furrowed in an upward tilt that begged for you when his lips were too preoccupied with moaning your name to do so. He just needed that final push to send him over the edge, and you knew you’d go tumbling down with him.

So you decided it was time to bring out the big guns, purring into his ear as he ground his hips against yours, “Be a good boy and cum for your Mommy?”

His hips stammer in their rhythm as he lets out a strangled moan that sounded more like a few consecutive gasps before he buried his face into your neck, gripping you to him as he rode the both of you through your orgasms with a low groan of, “Mmm, Mommy!”


	33. Gabriel - dating Gabriel and he discovers you have a kink for being tickled.

_**Warnings:** Kinks; NSFW_

Gif source:  (( _Unknown_ ))

> _Imagine dating Gabriel and he discovers you have a kink for being tickled._

———  _Request for anon_  ———

“Was that a moan?” Gabriel asks, giving you an amused look as he slows his tickling hands.

“Gabe, please,” you were breathing hard, face flushed for more reasons than the fact that your laughing had accelerated your heart rate, “If you keep this up…”

“What will happen?” he prompts as you trail off, a smirk fixating on his lips as he moves closer to you, before pulling you towards him despite your instinctual scooting away from his tickling. “Come on, tell me.”

Exasperated, you raise your voice through your laughter, confessing, “Tickling is a kink of mine, okay!”


	34. Dean Winchester - being engaged to Dean and since you can’t have a proper bachelorette party, due to your hunting lifestyle, Dean surprises you with booze and fun, but dorky, games. At one point he tells you that he got...

Gif source:  [Dean](http://megmeg-chan.tumblr.com/post/134378271217/theveryconfusedgirl-can-we-just-appreciate)

> _Imagine being engaged to Dean and since you can’t have a proper bachelorette party, due to your hunting lifestyle, Dean surprises you with booze and fun, but dorky, games. At one point he tells you that he got you a male stripper, only the stripper turns out to be him._

———  _Request for anon_ ———

“A stripper? Where have you been hiding him all this time?” you laugh, calling after him as he rushes from the room after having told you to wait right there for a second before the real entertainment of your makeshift bachelorette party.

As the music starts, you can’t help your giggles, the familiar sound of Def Leppard singing  _Pour Some Sugar On Me_ playing in the background as Dean reemerges just in time to seductively begin unbuttoning his shirt, “I’ve been hiding him in plain sight.”


	35. John Winchester, Sam & Dean Winchester - being in a relationship with all three Winchesters and Sam and Dean bickering about which of them you think is the best looking and who gives you the most pleasure during sex. When they decide to just ask...

**Summary for the Chapter:**

> **Warnings: NSFW; Incest**

_**Warnings:** NSFW_

Gif source:  [John](http://knoperps.tumblr.com/post/99060346124/jeffrey-dean-morgan-gif-hunt)  |  [Sam&Dean](http://megmeg-chan.tumblr.com/post/153336839982/devoiddean-celebrating-the-life-of-asa-fox)

> _Imagine being in a relationship with all three Winchesters and Sam and Dean bickering about which of them you think is the best looking and who gives you the most pleasure during sex. When they decide to just ask you, they realize you weren’t even paying attention because you were getting hot and heavy with Daddy Winchester._

———  _Request for anon_ ———

You’d abandoned their room in favor of John’s adjoining one as soon as the bickering looked to not be ending any soon. Sam and Dean hadn’t even realized your absence as they continued their heated debate on, in essence, which one of them you liked more.

When they finally do break from their circular arguing, Sam huffs, “Well, why don’t we just ask her, then?”

“Great idea; what do you think, (Y/N)?” Dean calls.

The only answer either of them get is the giggled, low moan of, “John,” from the other room, causing both brothers to curiously look in only to find you with John nipping down your neck as you straddled him on the bed.

You clearly had not paid attention to a bit of their arguing as you ask once realizing they were standing in the doorway of the adjoining room, “You boys want something?”


	36. John Winchester - Imagine riding John Winchester.

_**Warnings:** NSFW_

Gif source:  [John](http://megmeg-chan.tumblr.com/post/154755673817/mypapawinchester-jeffrey-dean-morgan-hand)

> _Imagine riding John Winchester._

——— _Request for anon_  ———

“Oh, so you want to be on top tonight, huh, darlin’?” John teases, giving you a crooked smile as he follows your hands on his chest upwards to catch your eyes with his.

“Yep,” you hum, leaning forward to capture his lips in a quick kiss that you break to chuckle, “I’m going to ride you tonight, and you’re going to let me.”

“I’ve got no objections to that.”


	37. John Winchester, Chris Argent - having a threesome with Chris Argent and John Winchester.

**Summary for the Chapter:**

> **Crossover: SPN & Teen Wolf**

_**Warnings:**  NSFW_

Gif source:  [Chris](http://alfella.tumblr.com/post/79369793165/we-are-the-teen-wolf-fandom)  |  [John](http://knoperps.tumblr.com/post/99060346124/jeffrey-dean-morgan-gif-hunt)

> _Imagine having a threesome with Chris Argent and John Winchester._

———  _Request for anon_  ———

“Please tell me you’re staying longer than a few days,” you breathe lowly, enjoying the heat of his breath and softness of his lips in contrast to the stubble surrounding them as John trailed kisses down your chest.

Chris slips the straps of your bra down as he easily removes the rest of the fabric while John answers, looking up at you teasingly, “We’ll see.”


	38. Crowley - Crowley wearing a kilt when he finds out men in kilts are a turn-on for you.

Gif source:  (( _Unknown_ ))

> _Imagine Crowley wearing a kilt when he finds out men in kilts are a turn-on for you._

———  _Request for pan-and-proud-writes_ ———

You nearly lost your composure when he showed up in a kilt, acting as if nothing was different after the initial couple of jokes from Sam and Dean. They had long moved on from their initial focus on his kilt, though you were struggling not to stare.

And that damn smirk Crowley was wearing let you know exactly what he was doing, though he couldn’t help from rubbing it in as he shoots your way, “See something you like, love?”

He very well knew you did.


	39. Balthazar, Peter Hale - Imagine Peter and Balthazar seducing you.

**Summary for the Chapter:**

> **Crossover: SPN & Teen Wolf**

_**Warnings:** NSFW_

Gif source:  [Peter](http://megmeg-chan.tumblr.com/post/150234962737/allsonargent-hes-basically-satan-in-a-v-neck)  |  [Balthazar](http://supernaturalgiffcs.tumblr.com/post/59316661311/gif-hunt-balthy) 

> _Imagine Peter and Balthazar seducing you._

———  _Request for anon_  ———

It wasn’t hard to bask in the attention the two of them had been giving you. Enjoying it came easy whenever Peter or Balthazar would flirt with you, sending warmth to heat a blush from you.

Until now, it hadn’t gone beyond playful flirting.

The tone changed thanks to you when you hummed suggestively, gesturing absently to the loft around you, “So, we have the whole place to ourselves?”

Peter’s lips quirked upwards, “Until Derek gets back later tonight.”

Balthazar raises a brow, “How much later?”


	40. Castiel, Crowley - a threesome with Castiel and Crowley.

_**Warnings:** NSFW_

Gif source:  [Here](http://megmeg-chan.tumblr.com/post/154307492387/itsokaysammy-who-are-you-people)

> _Imagine a threesome with Castiel and Crowley._

———  _Request for anon_  ———

“And this is what you want?” Castiel asks after your admission, or rather, Crowley’s coaxing of the truth from you with the little deductions of what your behavior around the two of them had possibly meant.

“Yes, but if either of you don’t—” you begin, only to get cut off by Crowley’s chuckle.

“Oh, love, have you not noticed the way the angel looks at you? It’s positively sinful,” that has you blushing as Castiel shifts his weight, his own blush creeping down his neck and telling you that what Crowley had noticed was true. Crowley continues, getting closer to you, “And as for me, well, I need no convincing, either.”


	41. Dean Winchester - giving Dean a lap dance/strip tease to ‘Pour Some Sugar On Me’ in the bunker.

_**Warnings:** NSFW_

Gif source:  [Dean](http://spnfans.tumblr.com/post/103926113460)

> _Imagine giving Dean a lap dance/strip tease to ‘Pour Some Sugar On Me’ in the bunker._

———  _Request for anon_  ———

_Take a bottle, shake it up  
Break the bubble, break it up_

“Sit down,” you urge as the music starts up, catching him as soon as he walked into his room with your lecherous smirk.

The look on Dean’s face told you you’d hooked him simply with your outfit alone. The singular request coming from your lips has him stammering out an obedient agreement before he does as you say and sits on his bed, eyes following the trails the curves of your body gives them as you run your hand down your neck and towards your chest seductively, Def Leppard blaring from the record player in the corner of the room.

_Pour some sugar on me_  
Ooh, in the name of love  
Pour some sugar on me  
C'mon fire me up  
Pour your sugar on me  
Oh, I can’t get enough


	42. Dean Winchester - you and Dean having sex to Demi Lovato’s ‘Body Say.’

_**Warnings:**  NSFW_

Gif source:  [Dean](http://megmeg-chan.tumblr.com/post/145731557062/laoih-dean-sex-dean-lydia-713)

> _Imagine you and Dean having sex to[Demi Lovato’s ‘Body Say.’](https://t.umblr.com/redirect?z=https%3A%2F%2Fwww.youtube.com%2Fwatch%3Fv%3DJca0B2lbqpU&t=OTc0YmNhYWIwMGExYjQyNTYxMDZlMzVjMWE2MGJmZTk0NzcxNTMxNyxYVmVzYzdqUw%3D%3D&b=t%3AuNoi0AujsProexVbD5JsWA&p=https%3A%2F%2Fthranduilsperkybutt.tumblr.com%2Fpost%2F154243301648%2Fwarnings-nsfw-gif-source-dean-imagine-you-and&m=0)_

———  _Request for anon_ ———

 _You can touch me with slow hands_  
Speed it up, baby, make me sweat  
Dreamland, take me there ‘cause I want your sex

Taking him home had been your idea just as much as it had been his, and now he was beneath you, the familiar sheets of your bed at his back as he grinned up at you with a mixture of excitement and arousal. Tonight, you were going to have it your way. Far be it from Dean to stop you.

His hands trailing up your waist slip around your back, finding the clasp of your bra by following the red lace straps as he flicks the deep green of his eyes back up to meet yours, knowing he didn’t have to ask permission thanks to the way you ground onto his lap in encouragement.

Still, you lick your lips in anticipation, whispering, “Do it.”

 _If my body had a say, I wouldn’t turn away_  
Touch, make love, taste you  
If my body told the truth, baby I would do  
Just what I want to


	43. John Winchester - letting John Winchester fuck you in the ass.

_**Warnings:** NSFW; I don’t think I’m too good at writing anal, but I tried!_

Gif source:  [John](http://megmeg-chan.tumblr.com/post/150954117862)

> _Imagine letting John Winchester fuck you in the ass._

———  _Request for anon_  ———

“Okay.”

One little word had brightened his whole day. In all honestly, this had an idea you’d entertained for a while, but had not quite had the nerve to act on it until he asked you. So now here you were, hovering above his lap as his lubed-up fingers slipped out of your prepared hole. God. Part of you worried if he would even fit despite the efforts that had been made over the last hour to get you ready.

John’s voice is low, thick with lust as you position his condom-wrapped length where you wanted it, “Take your time.”

You were practically jittering with nervousness and excitement, having to remind yourself mentally to relax as you give him one last glance before taking the plunge. With a breath you calm yourself and lower onto his tip slowly, feeling the lube aid in his entrance, yet still stretching you further than his fingers had as he fills you at your own pace. John grips at your thighs, holding himself back from thrusting up into the tight warmth that was you, but is unable to keep himself from the deep moan that comes from him the more you ease down upon him.

Once you have him fully sheathed, you raise and lower yourself in a few experimental thrusts, controlling your breathing as best you could as whimpers fought their way from your throat, soon turning into moans to mingle with his.

It takes one word from you to have him take the lead.

“Move.”


	44. Charlie Bradbury, Dean Winchester - being in a poly relationship with Dean and Charlie and them working together to get you to cum.

_**Warnings:**  NSFW_

Gif source:  [Here](http://talaraleya.tumblr.com/post/112711147612/my-mad-obsession-with-supernatural-month)

> _Imagine being in a poly relationship with Dean and Charlie and them working together to get you to cum._

———  _Request for anon_  ———

“Hey, double the manpower, double the reward, Winchester,” Charlie says, causing Dean’s grin to only get wider as he thinks over her naughty proposal. The two of them teaming up on you? He had to admit he liked the sound of it.

“Did she really say this was a turn on?” Dean asks, gesturing to the Renaissance costumes the two of them wore as they headed back to Charlie’s tent.

“She didn’t have to. I saw the way she drank you and me in. What do you say we give her what she wants?”


	45. Gadreel - being a demon and wanting to corrupt Gadreel, but it turns out he enjoys going bad. (NSFW requested)

_**Warnings:** NSFW requested_

Gif source:  [Gadreel](http://megmeg-chan.tumblr.com/post/142138975152)

> _Imagine being a demon and wanting to corrupt Gadreel, but it turns out he enjoys going bad. (NSFW requested)_

———  _Request for anon_ ———

“Don’t think I’m anything like you, demon,” Gadreel growls as he pushes you away from his kiss, against a wall. You grin despite his declaration, knowing you were much more similar than he wanted to admit.

“Why don’t you put what we are aside for the moment, hm?” you tempt, wrapping your arms back around his neck to pull him closer once more, knowing that with each of your attempts, his resolve breaks a little more. His corruption was the ultimate game for you, and you were having the most fun playing him, “After all, angels and demons can both enjoy themselves every now and then.”


	46. Gabriel - having sex with Gabriel while pregnant with his baby and him being all sweet.

**Summary for the Chapter:**

> **Warnings: NSFW; Pregnant!Reader**

_**Warnings:**  NSFW_

Gif source:  [Gabriel](http://megmeg-chan.tumblr.com/post/145848386972/happy-trickster-tuesday)

> _Imagine having sex with Gabriel while pregnant with his baby and him being all sweet._

———  _Request for anon_  ———

“Come here, beautiful,” Gabriel hums, pulling you closer as he urges you onto his lap, his fingers spreading over the curve of your stomach while he pushes the hem of your shirt upwards. His voice is low as he smirks at you, “I love you.”

You bend in to kiss him for a moment before he removes your shirt entirely, letting your smile break from his as you look down at him, “I love you, too, Gabe.”


	47. Castiel, Dean Winchester - having a threesome with Castiel and Dean.

_**Warnings:** NSFW_

Gif source:  (( _Unknown_ ))

> _Imagine having a threesome with Castiel and Dean._

———  _Request for anon_  ———

“Cas,” comes hoarsely from Dean’s lips as he tries his best to keep a shred of composure with your mouth where it is at the moment. Your fingers feel the twitch of his cock as you feel the angel move against your body, smoothing his hands over the curve of your rear as Dean chuckles, “Show our girl a good time.”

A warm kiss feathers at your shoulder, along with the scruff at Castiel’s jaw, a heated breath fanning across your skin as he breathes, “She is doing such a good job, isn’t she? It’s only proper to reciprocate.”


	48. Dean Winchester - Dean not caring that you’re on your period.

**Summary for the Chapter:**

> **Warnings: NSFW; Period sex**

_**Warnings:** NSFW; Period sex_

Gif source:  [Dean](http://megmeg-chan.tumblr.com/post/151420805267)

> _Imagine Dean not caring that you’re on your period._

——— _Request for Bixbi_ ———

“Dean,” you whine, pushing back his roaming hands with a laugh, “we can’t. I’m on my period.”

You expect him to pull back at that. To take the news of your monthly gift from Mother Nature with a frown and handle his business elsewhere like you had encountered with previous boyfriends. Instead, he quirks a brow, and chuckles as if he’s surprised that would be an issue at all.

“So?” Dean asks, “Unless it’s an problem for you, I’m still down.”

You grin at him, finally giving a nod, “Alright. Get a towel.”


	49. John Winchester, Sam & Dean winchester - Sam and Dean competing over who can make you have the best orgasm, but then John steps in and outdoes both of them.

**Summary for the Chapter:**

> **Warnings: NSFW; Incest**

_**Warnings:**  NSFW; Incest_

Gif source:  [1](http://megmeg-chan.tumblr.com/post/141811250882/saucynewf-ghostfacers-313-for)  |  [2](http://megmeg-chan.tumblr.com/post/150954032527)

> _Imagine Sam and Dean competing over who can make you have the best orgasm, but then John steps in and outdoes both of them._

———  _Request for anon_ ———

“So who was better, huh?” Dean asks, grinning from ear to ear as the blush that had covered his chest begins to subdue along with the labored breathing that had followed his orgasm, making Sam roll his eyes.

“It was me, wasn’t it? It’s alright, you can let him down gently,” Sam teases, his arm wrapped around your shoulders as you still try to come down from the orgasms you’d already had tonight. Now they wanted you to compare them? That wasn’t fair! How were you supposed to do that?

“I-I don’t know,” you scoff, hearing John’s glass clink against the table as he sets it down, along with the deep chuckle that has you looking down to the foot of the bed just in time for him to reach towards you.

“That’s because you’re both lousy, boys,” John notes, making the protests start from the men on either side of you as he pulls you from between them. His hands on your thighs guide you against him as he hums, “Let me show you how it’s done.”


	50. Dean Winchester - having been hunting with Sam and Dean for a while and having a friends-with-benefits relationship with Dean, and when he thinks it’s more than that, you have to set him straight. (Based on ‘Needed Me’ by Rihanna)

_**Warnings:** Mentions of NSFW content; Language (especially in the lyrics)_

Gif source:  [Dean](http://megmeg-chan.tumblr.com/post/150721273257/livingthegifs-just-how-i-imagined-by)

> _Imagine having been hunting with Sam and Dean for a while and having a friends-with-benefits relationship with Dean, and when he thinks it’s more than that, you have to set him straight. (Based on[‘Needed Me’ by Rihanna](https://t.umblr.com/redirect?z=https%3A%2F%2Fwww.youtube.com%2Fwatch%3Fv%3DRiexmXWoQZE&t=NTU3MmVjNzUyMmE1MzJkM2M0YjkxMjc2MzE4MTg2YjlhZmVkN2E5MixFOUFWZXZZYQ%3D%3D&b=t%3AuNoi0AujsProexVbD5JsWA&p=https%3A%2F%2Fthranduilsperkybutt.tumblr.com%2Fpost%2F151329301638%2Fwarnings-mentions-of-nsfw-content-language&m=0))_

———  _Request for anon_  ———

_I was good on my own, that’s the way it was, that’s the way it was_  
You was good on the low for a faded fuck, on some faded love  
Shit, what the fuck you complaining for?  
Feeling jaded, huh?  
Used to trip off that shit I was kickin’ to you  
Had some fun on the run though I give it to you

He was angry for no reason. Upset at you for going home with that guy you’d met at the bar the other night. Suddenly there were strings in the no-strings-attached-sex you had been having with him.

“Dean, baby,” you sigh, pulling him closer by snaking your arms around his neck, “you don’t own me. I’ll have my fun with whoever I want. I thought we were having fun.”

“We were,” he frowns. “We are.”

“Good,” you smile, patting him on the cheek as you give him a wink, “Then let’s not complicate things.”

_But, baby, don’t get it twisted_  
You was just another nigga on the hit list  
Tryna fix your inner issues with a bad bitch  
Didn’t they tell you that I was a savage?  
Fuck your white horse and a carriage  
Bet you never could imagine  
Never told you, you could have it


	51. Gabriel - having sex with Gabriel in public and nearly getting caught.

_**Warnings:**  NSFW_

Gif source:  [Gabriel](http://gifhunterress.tumblr.com/post/53856113999/richard-speight-jr-gif-hunt-185-please)

> _Imagine having sex with Gabriel in public and nearly getting caught._

———  _Request for anon_  ———

He had trailed after you out of the bar, abandoning the Winchesters for however long the two of you could take in this alleyway. You simply couldn’t wait any longer. Even though he could snap you into the confines of privacy in a single second, it still seemed too long to wait as his lips trailed down your neck.

Plus, there was the fact that the threat of getting caught turned you on a little bit. Okay, it turned you on a lot, if you were being honest.

And Gabriel had figured it out, his hand at the brick beside your skin as he hiked up your skirt with the other, your knee hooking around his hip to lock him against your body. He had figured you out and he was going to milk this newfound kink of yours for all it was worth. See just how far he could go before someone wandering from the bar could come upon the scene taking place in this alleyway, or worse, the Winchesters come looking for you.

Gabriel chuckles near your ear as you urge him on, hurrying him to just finish you off already, “Are you worried we’re going to get caught?”


	52. Benny Lafitte - letting Benny feed from you during sex and he’s completely careful about it.

**Summary for the Chapter:**

> **Warnings: NSFW; Biting; Blood**

_**Warnings:**  NSFW; Biting; Blood_

Gif source:  [Benny](http://bennylafitte.tumblr.com/post/134309118282/inacatastrophicmind-30-days-of)

> _Imagine letting Benny feed from you during sex and he’s completely careful about it._

——— _Request for anon_ ———

“You sure you know what you’re asking for, darlin’?” he asks, breathless, as you pull your hair out of the way of your throat, giving him a particularly enticing look as you bare your neck to him, all the while continuing to ride him slowly for your own pleasure.

You have him entranced, judging by the way his eyes drink you in, focusing on the heave of your chest before finding your throat, his fangs beginning to bite through the gum above his teeth, “Bite me, Benny.”


	53. Gabriel - your boyfriend, Gabriel, convincing you to make a sex tape with him.

_**Warnings:** NSFW_

Gif source:  [Gabriel](http://megmeg-chan.tumblr.com/post/145848386972/happy-trickster-tuesday)

> _Imagine your boyfriend, Gabriel, convincing you to make a sex tape with him._

———  _Request for anon_  ———

“I bet you’d look great on camera,” he purrs near your ear, trying to convince you to give into his suggestion of making a sex tape with him.

“But if anyone else sees…” you begin, only for him to calm any worries of it getting out with a chuckle.

“Trust me, no one else will see it.”


	54. Crowley, Dean Winchester - losing your virginity in a threesome to Crowley and Dean.

**Summary for the Chapter:**

> **Virgin!Reader**

Warnings: NSFW

Gif source:  [Both](https://t.umblr.com/redirect?z=http%3A%2F%2Fdark-spn-angel.livejournal.com%2F94724.html&t=NjI0M2NkYTU5NjhlNTgyMmQ2NDE4NTdiMjkyOWFlYWM0ODg1YWJlMCxEZXdzOHdVZg%3D%3D&b=t%3AuNoi0AujsProexVbD5JsWA&p=https%3A%2F%2Fthranduilsperkybutt.tumblr.com%2Fpost%2F150131168758%2Fwarnings-nsfw-gif-source-both-imagine-losing&m=0)

> _Imagine losing your virginity in a threesome to Crowley and Dean._

———  _Request for anon_ ———

“Dean, this isn’t you,” you begin, backing away from him as he takes a step forward.

“Oh, it’s all me, honey,” he smirks, more forward than he’d ever been with you in all the time you’d known him. Yeah, you’d always had a thing for him, but you weren’t really the most seductive person in the world, and had managed to cling onto your virginity up until this point. That said, it had never been any secret that you found Dean attractive.

The big secret you had kept had been how you’d wanted the King of Hell, who was standing beside Dean, just as much.

This was such a bad idea, but as Crowley and Dean corner you between them, you find yourself wanting to do as Crowley asks when he practically purrs, “Give in, love. What are you waiting for?”

Surprising yourself, you hear a single word pass your lips as you realize aloud, “This.”


	55. John Winchester - being a college girl and going home for break and bringing your boyfriend, John Winchester, with you, so you have to convince your disapproving mother that he’s just a friend while he secretly repairs your broken bed just so the...

**Summary for the Chapter:**

> **Warnings: NSFW; Age gap**

Gif source:  [John](http://megmeg-chan.tumblr.com/post/149451698042)  |  [CollegeGirls](https://t.umblr.com/redirect?z=http%3A%2F%2Frebloggy.com%2Fpost%2Fmine-the-vampire-diaries-elena-gilbert-tvd-caroline-forbes-bonnie-bennett-mine-t%2F63066634187&t=YmVjNzRmZTllNmVhNzdjNmUzMjA4NmEwMzlmYTRiYTZlNmFkYjJmYywzRjVpcWpnYQ%3D%3D&b=t%3AuNoi0AujsProexVbD5JsWA&p=https%3A%2F%2Fthranduilsperkybutt.tumblr.com%2Fpost%2F149991012328%2Fgif-source-john-collegegirls-imagine-being-a&m=0)

> _Imagine being a college girl and going home for break and bringing your boyfriend, John Winchester, with you, so you have to convince your disapproving mother that he’s just a friend while he secretly repairs your broken bed just so the two of you can break it all over again._

———  _Request for Bixbi_  🙇🏻 thank you 🙇🏻———

_“She honestly would not even let you in the house if she thought you were my boyfriend,” you had sighed, falling back on your dorm’s bed as John chuckled beside you. He wanted to come with you when you visited your mom this weekend, but there was just one problem: she was a total hard-ass about any of the guys you’ve ever dated, and him being older did not help your case._

_“Let’s just tell her I’m a friend of yours, then,” he’d suggested, hand reaching out to comfortingly rub your thigh and get you to look up at him, “at least until she warms up to me.”_

The ‘just friends’ ruse you’d cooked up had been falling apart ever since you set foot in your mother’s apartment, yet somehow by Sunday she managed to stop watching you like a hawk for at least long enough to go and get groceries for dinner, "I’m headed out!” Your mom’s call of your name has you peeking your head out of your bedroom, where you had been trying to help John fix the falling-apart bed that past-you had said was future-you’s problem before you’d left the last time you came to visit. “Anything you want from the store?”

“No thanks, Mom! Be safe!” you reply, watching from the small hallway of the apartment that had a straight view to the front door as she left, still giving you a warning look, and locked the door behind her.

You don’t realize the warning look was to John who had peeked out of your bedroom, as well, until you turn around at his whisper of, “Is she gone?” The look on his face is just as wanting as yours as you hold up a single hand for a minute, listening for any sound of her re-arrival into the apartment before the two of you retreat back into the bedroom for more than fixing your bed.

“Give it a minute.” 


	56. John Winchester, Sam & Dean Winchester - having a foursome with John, Dean, and Sam Winchester.

**Summary for the Chapter:**

> **Warnings: NSFW; Incest**

_**Warnings:** NSFW; Incest_

Gif source:  [John](http://megmeg-chan.tumblr.com/post/149452850717/fuckyeahjeffreydeanmorgan-gifsbysimplysonia)  |  Dean ( _Unknown_ )  |  [Sam](http://gifsofsam.tumblr.com/post/64238341257/x)

> _Imagine having a foursome with John, Dean, and Sam Winchester._

———  _Request for anon_  ———

You watch over Dean’s shoulder as John sheds his shirt, admiring the view of you sandwiched between the two younger Winchesters. Sam’s lips on your neck practically consume your senses as two sets of hands work in unison to strip you bare of the clothing that had been feeling too tight ever since you’d heard you’d be spending the night with all three of them. Thank God that the motel only had one room left.

“Lets enjoy her, boys,” John clears his throat as he moves closer just as Dean lowers his lips to your breasts, hands caressing and making your back arch against Sam’s chest.

Sam breaks away from the spot he’d been abusing on your neck, definitely leaving a bruise to form in a few hours, “I plan on it.”


	57. Dean Winchester - Dean giving you a strip tease and you can’t keep a straight face.

_**Warnings:** NSFW? Just in case…_

Gif source:  [Dean](https://t.umblr.com/redirect?z=http%3A%2F%2Fwww.thenerdpirates.com%2Fblog%2Fnobody-hates-you-more-than-you-do-thoughts-on-dean-winchester-and-self-contradiction-supernatural&t=NmU3NjZkZWQ1ZTE5NmM1YzI2MTEzNDNiN2VmMTY2YTRlZmI0NjRlMSw5Zk52dXp0Wg%3D%3D&b=t%3AuNoi0AujsProexVbD5JsWA&p=https%3A%2F%2Fthranduilsperkybutt.tumblr.com%2Fpost%2F149590229683%2Fwarnings-nsfw-just-in-case-gif-source-dean&m=0)

> _Imagine Dean giving you a strip tease and you can’t keep a straight face._

———  _Request for anon_  ———

“What are you doing, Dean?” you chuckle from the seat you had on his bed as ‘Cherry Pie’ blared from the record player that had a Warrant album spinning on it.

He over-the-top seductively turns towards you, hint of playfulness in his eyes as he replies, “You just sit there and enjoy yourself, alright?” Dean’s hands slip to the hem of his shirt as he begins to pull it up his body before shucking it over his head as he moved closer to you on the bed, “Liking what you’re seeing?”

Your grin’s wide while you try to stop the giggles from bubbling up in your throat as his hands slip to his belt with the sway of his hips, the stress from the day hardly an afterthought after the man in front of you began stripping, “Definitely.”


	58. Dean Winchester, Gabriel - having sex with Gabriel and Dean in a bouncy castle.

_**Warnings:** NSFW_

Gif source:  [Here](https://t.umblr.com/redirect?z=http%3A%2F%2Frebloggy.com%2Fpost%2Fchristmas-supernatural-gabriel-trickster%2F38084679235&t=ZmEwODc5Y2Q5NWNlNDdkN2YxZjhhZDE1ODFmYWUwMTRiODk1ZjQ0MCxpcURyZ0FNNA%3D%3D&b=t%3AuNoi0AujsProexVbD5JsWA&p=https%3A%2F%2Fthranduilsperkybutt.tumblr.com%2Fpost%2F149340782550%2Fwarnings-nsfw-gif-source-here-imagine-having&m=0)

> _Imagine having sex with Gabriel and Dean in a bouncy castle._

———  _Request for anon_ ———

You had wanted to go to a carnival, so leave it to Gabriel to get you in after-hours. One bouncy castle and an excited entrance later, you were laughing through the black netting towards the angel and hunter who had come along with you.

“You know that’s for kids, right?” Dean chuckles, making you give him a suggestive look as you stop your bouncing long enough to lean towards the edge of the castle.

“How ‘bout we make it more adult-friendly, then?”


	59. Sam Winchester - taking your virginity.

**Summary for the Chapter:**

> **Virgin!Reader**

_**Warnings:**  NSFW_

Gif source:  [Sam](http://megmeg-chan.tumblr.com/post/137063899092/im-just-sayingi-think-a-smut-apocalypse-would)

> _Imagine Sam Winchester taking your virginity._

———  _Request for pietremximoff_  ———

“First time, huh?” Sam chuckles, making your blush deepen that you’d been so easily pegged.

“Ah, am I that awkward?” you ask, insecure for just the moment it takes for him to dissuade your worries.

“Not awkward… Just inexperienced,” Sam takes the chance to press his lips against your sweetly, but as he pulls back the look in his eyes is filled with a lusty excitement, “But that can be fixed.”


	60. Crowley - having sex with Crowley for your anniversary and your brothers, Sam and Dean, catch you in the act.

_**Warnings:** NSFW_

Gif source:  [Crowley](http://megmeg-chan.tumblr.com/post/142167046687)  |  [Brothers](http://megmeg-chan.tumblr.com/post/142485319457)

> _Imagine having sex with Crowley for your anniversary and your brothers, Sam and Dean, catch you in the act._

———  _Request for anon_  ———

“Sam, I need you to do me a favor,” Dean begins as he shuts the door to your bedroom just as quickly as he’d opened it, looking towards Sam who looked just as scarred as he felt. “I need you to hold me down, and pour bleach into my eyes, okay, because I can never forget what I’ve just seen!”

“Oh, shut it!” Crowley calls through the door, as you lose yourself in laughter, still seeing the shocked looks on your brothers’ faces as they walked in on the two of you having sex.

Sam shudders, “I’ll grab the bleach.”


	61. Sam Winchester - being Alex’s friend from nursing school who knows all about the supernatural and hunters, and you meet Sam when he’s visiting Jody and the girls in Sioux Falls with his brother, only to wind up in bed with him.

_**Warnings:**  NSFW_

Gif source:  [Alex](https://megmeg-chan.tumblr.com/post/181511701117/frozen-delight-13x10-wayward-sisters-my-love)  |  [Sam](https://megmeg-chan.tumblr.com/post/175938112362/impala-dreamer-sgarrett49-sending-you-so)

> _Imagine being Alex’s friend from nursing school who knows all about the supernatural and hunters, and you meet Sam when he’s visiting Jody and the girls in Sioux Falls with his brother, only to wind up in bed with him._

———  _Request for anon_  ———

“Alex, hey,” you watch as a giant of a man greets Alex as you round the corner into the living room of Jody’s place. You feel your heart pick up, there was no denying just how attractive he was, his hair falling a bit into his face as he bent slightly to embrace her.

“Sam? What are you doing here? Is Dean with you?” Alex pummels him with the questions, giving him a familiar side-hug that leaves you acutely aware that there was nothing romantic going on between your friend and  _Sam_.  _He was free game._

Sam’s dark eyes flick to you, acknowledging your presence with a brief, “uh,” before Alex cuts him off. You almost think you’ve seen him check you out for a second, before you focus in on what Alex was saying.

“Oh, this is (Y/N), a friend from school. She already knows about what we do, so, spit it out. You guys here for a hunt?”

“Yeah, we are. There’s some wendigo activity in Harrisburg, we think,” he rubs the back of his head with an almost awkward chuckle before greeting you with an outstretched hand. “Anyway, it’s nice to meet any friend of Alex’s. I’m Sam Winchester.”

You take his hand in yours, trying not to notice just how large it was or how strong his grip seemed to be as you gave him a shake, “It’s nice to meet you, too. Heard a lot about you and your brother from the girls.” His hand lingers in yours a bit longer than necessary, before you let go.

“Nothing too bad, I hope,” Sam smiles at you, and  _fuck_ even his teeth were perfect. You try to force down the electricity his gaze sends buzzing through you, or the way you would like to think his smile was a little flirty. “Are you staying for dinner? I’m just saying, I doubt Jody will let you escape without it.”

“I think I can stay an extra hour or two.”

“Good,” Sam hums, and you know you’re not seeing things this time. He definitely was flirting with you. You were even feeling bold enough to flirt back.

Maybe it was the beer you had with dinner, or maybe it was the simple fact that you found Sam Winchester absolutely gorgeous, but either way, when he offered you a ride back to your place at the end of the night, you accepted. You don’t know what his excuse was, but when you offered him to come in, he accepted.

"I don’t usually do this,” you murmured against his lips, as he walked you back against the wall of your apartment. Another kiss separated the continuance of your statement, forcing a pause before you add, “take men I’ve just met home with me.”

Sam chuckles, his hands grasping at your thighs and tugging them up around his waist, “I’m glad you made an exception, then.”


	62. Castiel - doing research in the library with the boys and Cas, but all you can do is think about how amazing he looks, which leads to dirtier thoughts, and Castiel accidentally reads your thoughts because they’re just so...

**Summary for the Chapter:**

> **Warnings: NSFW; Grace kink**

_**Warnings:**  NSFW; Grace kink_

Gif source:  [Cas](https://megmeg-chan.tumblr.com/post/173983717707/splendidcas-babydaddymish-was-that-really)

> _Imagine doing research in the library with the boys and Cas, but all you can do is think about how amazing he looks, which leads to dirtier thoughts, and Castiel accidentally reads your thoughts because they’re just so damn loud, so he stealthily gets you off with his grace._

———  _Request for anon_  ———

The text in front of you was thick, ancient, and fraying at the seams. Clearly, despite the Men of Letters’ attempts to preserve it, it had seen better days. You gingerly turned to the next page with a sigh, searching for anything that could help you find a way to get Mary and Jack back.

The boredom and eye fatigue gets the better of you for a moment when your eyes glance from the book to the angel across from you. Castiel was immersed on the internet, which, ironically enough, he had become quite proficient with. You all doubted there would be much to find about this topic online, but Sam and Dean had insisted at least two of you look it up, and so Cas was handed the job, with Sam working away on his own laptop. To you and Dean were left the books, which you both had groaned about.

Your mind wanders along with your eyes, down the neck of the angel, observing the stubble that trailed there. He looked the same as always, in his trench and suit, though you find yourself wishing he were wearing a few less layers at the moment. The look of concentration on his face shouldn’t have lit the fire in your belly that it did, but with how his index finger ran along his lips absentmindedly, you found yourself dwelling on just what else he could be doing with those lips— with those hands— instead of sitting across from you doing research.

And you’re lost to your own thoughts, eyes glazed over as you stare down at the book you were certainly not reading anymore, far preferring your own fantasy to the Old English that littered the pages before you. You’re engrossed in the image of straddling Castiel while he kissed down your neck, his lips traveling along your breasts as his hands kneaded the flesh of your ass, leading you to rock gently in his lap, just enough to tease your core against the hard-on that pressed on the other side of his trousers.

Your tongue darts out to wet your suddenly dry lips, swallowing calmly as you think further on the fantasy, which suddenly takes a turn towards you riding his thigh in the very seat he was sat in now. You would grip at his shoulders as he steadied you, rocking yourself in a desperate pursuit for the friction that would sufficiently sate your craving for him. You shift in your seat, crossing your legs in an attempt to deny the stirring of lust in your core, but your mind still betrayed you. Would he make you beg, you wondered?

You’re brought from your fantasy by the feeling of eyes watching you, causing you to instinctively glance up from your book. Blue eyes pierce into you, and you find your whole body heating, as if you weren’t already wet enough between your thighs. Meekly, you offer Castiel a smile. Shaking off the slight worry that his gaze was a bit  _too_ knowing, you look back down to your book with a soft sigh that goes unnoticed by the Winchesters. You needed to get back to work, and the idea of Cas bending you across the table was stalling your every thought.

You shift, feeling a slight tickle at your thigh, reaching down to rub the area in the assumption that it was a simple itch. The feeling only continues, warming slowly, a humming, vibration that slips between your thighs, causing you to stiffen as you begin to realize just what it was. When the feeling covers your core, settling to buzz right against your clit, you look up, wide-eyed at Castiel.

_He wasn’t_.

But the smirk that lined his lips told you that, yes, he  _was_. It was hidden behind that same finger that had been pressed against his lips moment ago, but there it was. He didn’t even look up from the computer at you as the feeling intensified, a pressure slipping through your folds and into you, lighting you with a lust and heat that you couldn’t control.

You bit down on your lip, desperate to keep your breathing even as you willed yourself not to spare a single glance at either of the Winchesters. They were clueless as to what,  _exactly_ , Castiel was doing to you, and you wanted it to stay that way.

He wasn’t going to make it easy on you, though.

You nearly gasp aloud as you feel his grace curl within you, a hot, vibrating energy pressing within the deepest parts of your core, and buzzing against your clit so deliciously that you couldn’t keep your mouth from dropping open just slightly. You glare at him over your book, catching Castiel’s eye this time, and damning his smirk.

He was going to make you cum right here in front of them.


	63. Castiel, Dean Winchester - having been in an unlabeled relationship with Cas before he ran off to protect Kelly, and after months of bottled up hurt and anger at him for leaving you without a second thought, you wind up in bed with Dean.

**Summary for the Chapter:**

> **Warnings: NSFW; Adultery/cheating? Definitely angst, for sure.**

_**Warnings:**  NSFW; Adultery/cheating? Definitely angst, for sure._

Gif source:  [Castiel](https://megmeg-chan.tumblr.com/post/181518764217/endiness-i-understand-why-she-trusted-you-why-i)  |  [Dean](https://megmeg-chan.tumblr.com/post/181518693257/supernaturalfreewill-concerned-and-cautious-dean)

> _Imagine having been in an unlabeled relationship with Cas before he ran off to protect Kelly, and after months of bottled up hurt and anger at him for leaving you without a second thought, you wind up in bed with Dean._

——— _Request for anon_  ———

The churning cauldron of emotions only grew when Dean pushed you back gently, by his hands on your arms, as if coming to his senses past the way he had been kissing you back a moment before, “Wait, we can’t do this. You don’t want to do this. Not really.”

“I do, Dean,” you didn’t care if you sounded like you were begging, or pleading with him. You wanted— needed something that was going to take these past few months off your mind, if only for a little while. Something that would take  _Castiel_ off your mind. You know you sound pathetic, but there’s a bit of desperation in him, too, and you’ve never hidden anything from Dean before, so you weren’t about to start, now, “ _Please_.”

“You’ll regret it. When we find Cas—”

“Do you see Cas here?” you snap, anger icing your voice into a sharp edge that quiets Dean for a moment. “Cas is gone! He didn’t even take one single second to think about me before he left, so that just shows how much I mean to him. We never even talked about what we were, so what did I expect? Of course I was  _nothing_  to him.” You surge forward, your lips pressing against Dean’s roughly, and you know it takes all his strength to deny you a second time. You doubt he can do it a third.

He says your name, his tone a warning; a final chance to take this back— to not go through with what you both needed right now. There was no doubt that he, too, was left hurt with Castiel’s abandonment, and he sympathized with you enough that this was his last protest. His last out he was going to give you.

“Dean,” you murmur, your fingers carding through the short buzz at the back of his head, before you grip against the longer hairs at the crown of his head, “make me forget about Cas,  _please_.”


	64. Castiel - you and Castiel being each others first.

**Summary for the Chapter:**

> **Virgin!Reader; Virgin!Castiel**

_**Warnings:** NSFW_

Gif source:  [Castiel](https://megmeg-chan.tumblr.com/post/174012945317)

> _Imagine you and Castiel being each others first._

———  _Request for[@godofallthefuckingsrepents](https://tmblr.co/mm_6uPEkyGjd9xEJV2kX9tw) _———

You liked to think you  _weren’t_ some shy little virgin that had never seen a naked man before. You didn’t have that luxury, living with the Winchesters and risking your life on a day-to-day basis. Those boys had stripped down for you to patch them up and you had done the same more times than you could count. Dean openly talked about his minor porn addiction, to which you and Sam would either curl your noses up at or tease him on it, and you hadn’t been a stranger to slipping your fingers into the band of your panties on frustrating occasion. You  _were not_ naïve about sex.

So you really shouldn’t be as nervous as you were right now. You shouldn’t have been so on edge from simply brushing your lips against the stubble along his cheek, or felt your body heat up to an unbearable temperature as your breath hitched in your throat at the sight of him sitting, shirtless, before you.

“There, better,” you breathe, watching as Castiel’s eyes slipped to yours and darkened a bit in a way you had never seen on this angel before. Sure, you had been leveled with that look from unsavory men in bars before, but never Cas.

“What was that for?” Castiel murmurs, just as quietly and seemingly on-edge as you were, and you find yourself wondering if he felt the electric undercurrent of tension that had sparked in the room.

You gesture to the scratch on his cheek, something you had just cleaned and wasn’t healing properly with his diminished grace, “Oh, it’s something we do— humans, I mean. Kissing it better.” God, did you sound as awkward as you felt when you laughed a bit in an attempt to lighten the mood. Your body betrayed you as your eyes slipped to his lips, which you were far too close to, still leaning against him slightly with the hand you placed on his shoulder for leverage still lingering there. They were chapped, but full, and your mind wandered to what it would feel like for him to kiss you.

“I have more injuries,” Castiel begins, swallowing a bit as he catches your eye once again. “Are you going to ‘kiss them better,’ too?” It was a genuine question, something he wanted to know, but you don’t mistake the way his own breathing quickens, or how his eyes have dilated in the few moments you’ve sat so close to him. He wasn’t a master at flirting, or coming onto a woman. You doubted he’d ever been with one before, either.

So you dare to say it. To look him straight in the eyes and allude to what you really wanted to do to him.

“I’ll do more than give you a kiss, if you want me to, Cas.”


	65. Castiel - admitting to your boyfriend, Castiel, that you really want him to be rougher with you in the bedroom, unleashing a really kinky side of him that you hadn’t known he had.

**Summary for the Chapter:**

> **Warnings: NSFW; mentions of rough sex, choking, etc.**

_**Warnings:** NSFW; mentions of rough sex, choking, etc._

Gif source:  [Castiel](https://megmeg-chan.tumblr.com/post/129960602942/deanskitten-but-what-the-fuck-is-that-little)

> _Imagine admitting to your boyfriend, Castiel, that you really want him to be rougher with you in the bedroom, unleashing a really kinky side of him that you hadn’t known he had._

———  _Request for anon_  ———

You knew you should have been content. Your sex life was amazing as it was, full of passionate lovemaking that had one hell of a buildup and could leave you breathless, but there was a part of you that was left unsatisfied after your relationship with Castiel turned physical. He was an amazing lover, no doubting that, but sometimes you wanted something a little less vanilla than slow missionary.

Trying to explain the deep, primal need in you to have your sweet, caring, angelic boyfriend bend you over and fuck you hard and rough was proving more difficult than you anticipated. Your own fear crept up in the back of your throat, that he would question just what had made you the way you were, or worse, that he would take your suggestion as an accusation that he was doing something wrong in the bedroom.

You were not rehearsed, stammering over your words as you averted your eyes from having to admit your confession directly under his steel blue gaze, “I just… want it rougher sometimes, Cas.”

“Rougher,” Castiel repeats— almost in a question, but not quite— as if he were rolling the idea on his tongue, scrutinizing your embarrassed plea. “Could you explain to me just what that entails?”

_God_ , this was a bad idea. Why did you even open your mouth? You couldn’t even look at him as you felt yourself heat up to your ears. How were you supposed to explain what rough sex was?

Taking a breath, you let yourself fall back on the many fantasies you’d had involving just what Cas could do to you if he really put his mind to it. Which one should you tell him, first?

“Uh,” what an eloquent start, “maybe you could just, you know, like fuck me harder… grab me harder… bend me over sometimes… choke me a little…?” The suggestions sounded meeker the more you went on, until, finally, you dare to look at him.

It’s then that you notice the slight upturn to Castiel’s lips and the amused glint in his eye, before he urges, “Go on.” The  _bastard_ was teasing you. Before you can become annoyed at the realization, he moves on the bed, dipping you into his side as it shifts with his weight, which is all the leverage he needs to take the upper hand and push you down into the mattress. “You seem to have thought about this at great length.”

You let out a huff at the sudden movement, a shiver of excitement going through you at the feeling of his hands keeping your wrists captured on either side of your head, so firmly you had no hope of escaping his hold, “Cas… I have.”

He ruts his hips against yours roughly, letting you feel the hard-on that had been previously so well concealed by his trousers and drawing a gasp from your lips, “Good, because I have some ideas of my own.”


	66. Sam & Dean Winchester - Imagine being in a poly relationship with Sam and Dean Winchester and being pregnant, but your pregnancy hormones making your horny all the time, so they both try to keep you satisfied.

**Summary for the Chapter:**

> **Pregnant!Reader**

_**Warnings:** NSFW; Pregnant reader_

Gif source:  [Here](https://megmeg-chan.tumblr.com/post/173621488212)

> _Imagine being in a poly relationship with Sam and Dean Winchester and being pregnant, but your pregnancy hormones making your horny all the time, so they both try to keep you satisfied._

———  _Request for anon_  ———

A month ago, Dean had teased that this particular symptom of your pregnancy was a blessing in disguise, but now, you knew good and well that you were wearing your boys out— especially when, some days, you could hardly keep your hands to yourself.

Today was one of those days.

In your own defense, Dean had started it this morning, when he’d joined you in the shower. That round was his own fault. Then, as he was cooking breakfast, you found yourself taking Sam to bed. Researching the case focused your energy elsewhere, for a time, up until you were walking back into the library to find Sam, looking far more delectable than should be legal, and you felt a familiar warmth trickle through you.

You didn’t even care that you would be interrupting them, at this point.

“Sammy,” you began, your hands moving from his shoulders to smooth down his chest as you look over his shoulder to the laptop in front of him, “have you found anything, yet?”

He straightens up a bit in his chair, and you hear his shaky breath as your lips press against the side of his jaw, just below his ear, “Uh, not yet,” he pauses, swallowing and no doubt glancing across the table at Dean, before continuing in a slightly huskier warning, “and I’m not going to if you don’t stop that.”

“Do you want me to stop?” you hum, right before abusing his neck with your lips and tongue, no doubt to leave a quite visible love bite there in the future. The groan he gives goes straight between your legs, leaving you aching for something more tangible. Breathy, you whisper, “I don’t want to.”


	67. Dean Winchester, John Winchester - you’re only a little younger than Sam and have been hunting with the Winchesters ever since you were a teenager, after John saved you, but you fell in love with John, and confessed your feelings and slept with him...

_**Warnings:**  Mentions of NSFW events (just in case); angst_

Gif source:  [John](https://megmeg-chan.tumblr.com/post/160439098432)  |  [Mary](https://megmeg-chan.tumblr.com/post/182184387227/veryamooseing-supernatural-12x06-celebrating)  |  [Dean](https://megmeg-chan.tumblr.com/post/168597242332)

> _Imagine you’re only a little younger than Sam and have been hunting with the Winchesters ever since you were a teenager, after John saved you, but you fell in love with John, and confessed your feelings and slept with him right before he died. You grieved him and wound up moving on years later with Dean, determined to take the fact that you once had a thing with John to your grave, but then John gets brought back, and him and Mary reunite, and he finds out that you’re with Dean now._

———   _Request for anon_   ———

You felt like you couldn’t breathe. You were desperate to escape his presence, to escape his eyes boring into the back of your skull as you sat, centered between Sam and Dean in the front seat, straddling the console with Dean’s right hand resting, familiarly, on your thigh. Usually, Dean’s touch would relax you— everything you needed to calm your nerves and center your focus.

Not now, though. Not with John’s eyes on you. Not knowing what you did— what only the two of you knew.

You barely gave Sam the time to scoot out of the impala’s passenger side before you’re scrambling after him, your boots hitting the dirt hard as you round the back and wrench the trunk open. You needed to kill something. Do something to get this tension and anxious energy out of you.

God, you hadn’t spoken more than two words to the man since he’d been… resurrected? Was that the word? Coming back to life seemed to run in the Winchester family, it seemed.

But you’d never expected to see those dark, brown eyes again. To have them looking at you as if you weren’t a day older than the twenty-one year old you’d been when he’d died. As if it were just yesterday that he had been all you needed.

With a breath, you pass out the guns to the boys— your  _family_. First Sam, then Dean. Mary comes up third, and you do your best to not look her in the eye. You hadn’t felt it until after John came back, but now you felt guilty— dirty. As if you were  _the other woman_ , even though you knew you hadn’t been. You don’t look at John either as he takes the shotgun you offer from you, despite how hard he tries to make eye-contact.

“Hey, lock baby up good for me, babe,” Dean calls, drawing your attention.

You desperately hope your smile was believable, “Y-Yeah! Do you even have to ask?”

“Gotta’ take care of my two best girls!” he shoots back a wink, playful, oblivious to the tension in your shoulders. For that you’re grateful.

John is not as oblivious. He lingers back with you as Sam, Dean, and Mary trail ahead, which isn’t any good for the growing knots in your back, the tension tying your muscles up in ways that you’re certain a good massage wouldn’t even be able to work out.

“We need to talk,” he murmurs lowly.

“No, we really don’t,” you keep it quick, low, still avoiding looking in his direction.

You quicken your pace, only for John to match your steps, and you slow up again when he adds, sounding nonchalant, as if there wasn’t something simmering beneath his words, “So, you and Dean, huh?”

“You were dead,” you hiss at him. “You don’t get to say that.”

“Just… didn’t figure you would move on so quick, darlin’,” but there’s an edge to his tone, too, and the first time you look him in the eyes today is to glare at him.

“Me and Dean didn’t get together until after he was, and then wasn’t a demon,” you grit out, trying to stay as quiet as possible.

“Dean was a demon?” John’s brow furrows, and you shake your head at having forgotten that he wouldn’t know the same timeline you do.

“Yeah,” you leave it at that, instead focusing on the back of Sam’s head in the distance, until you can’t anymore. “We shouldn’t even be talking about this.”

“You want to pretend like it never happened?” John stops walking, which sparks a panic in you that he’d attract the attention of the three in front of you, but you stop in front of him regardless of that fear. Following after John Winchester like you had all those years ago. John whispers quickly to you, “Like I wasn’t the closest I’d been to happy since Mary with you?”

“Don’t say that, John. You  _can’t_ say that. Not now. Now, I have Dean. Hell, you have Mary back, which is what you wanted all along,” you fight the burning in the back of your nose that threatens to release tears. “Be happy, with her.”

You watch as John’s eyes flick back and forth, searching yours for something, before he asks, “And you’re happy with Dean?”

“Hey, what’s the holdup?” you hear ahead, making you force a smile and wave back to Dean.

“Sorry! Got caught up in catching up!” you lie easily through your smile. Something else John taught you to do. Turning away from him, you keep your voice low enough for only him to hear, “I’m as close to happy as I’ll ever get, John.”


End file.
